The Long Trail Back

I just spent nearly five months walking. I walked every day - sometimes just a few (~10) miles, and some days 30 or more. It was difficult at times, fun most of the time, and rewarding with every step.

When you walk that much your sense of time changes. I rarely knew what day it was - or even what month it was. I lost all knowledge of days of the week. I thought about little other than miles, resupply, water carries, and camping spots.

The trail provides. It gives you what it gives you, and it gives you what you need. My job was simply to keep going.

I started the Pacific Crest Trail in April and walked from Mexico to Canada, crossing deserts, forests, mountains, snow fields, rivers, blown down trees, and more changes in weather than I can list. I saw more sunrises and sunsets than I have in years. I saw an amazing number of stars and animals. And I learned more about patience than I ever thought I needed to.

Now that I’m home - clean, rested, and only slightly re-civilized, I’m realizing the harder part isn’t finishing the trail. It’s what comes after.

Letting Go of Momentum

In my past jobs, I’ve always been fueled by momentum. I like the complexity of projects that make a difference, teams that kick ass, and systems that bring it all together. I build cultures of continuous improvement and learning that only comes with a constant forward motion.

This summer, I learned that the trail doesn’t reward speed - It rewards consistency. The difference between 20 and 30 miles a day isn’t strength - it’s sustainability. Every time I pushed for “big miles”, I did them - but paid for it with fatigue and the blahs the following day. I found that the sweet spot isn’t about doing more - it’s about finding a rhythm that works and keeping it going. I kept my daily mileage and pace sustainable, and I was persistent. I walked, and I got pretty good at it.

That same mindset is guiding my eventual return to work. For the first time in decades, I have the space to selectively choose what’s next. It’s tempting to treat the job search like another big trail day, but now I know better.

This time, it’s about deliberate and selective steps toward meaningful work - and even in this market - not about “just” finding a job.

The Weight We Carry

My pack was relatively light when I started, but it got lighter. Over time, I ditched a pillow, camp shoes, and eventually my Kindle (I did read four books on trail first). Every other piece of gear in my pack was actively used. There was nothing extra - just what I needed to support my walking habit (including food, shelter, and the bare minimum of clothing).

In work, we accumulate tools, habits, and expectations that made sense at one time, but now may just weigh us down. We think busy equals valuable. We confuse structure with safety. On trail, you can’t afford that. You only carry what you really need.

As I look toward my next role, I ask myself, “What still earns its place? What roles, rhythms, and relationships can carry me from where I am now forward, and which are just extra ounces of uggh that I would rather not take on?”

I want to work with people who care about clarity, not noise. Teams where transparency, accountability, and psychological safety are culture. I want to work with people that care as much about learning and growth as they do about great software engineering. I’m at a stage in my career where I don’t want to deal with bullshit. When I hiked, I only carried the absolute essentials. I care about building great teams who build great software. I’m not interested in carrying any unnecessary weight.

Learning to Trust the Trail

One of the strangest parts of a long hike is how little control you have. Fires can close sections or reroute you. Snow hides the trail. Injuries force shorter miles or rest days. Sometimes water is flowing to your waist - on other days you have 20 miles between any drinkable water. You plan, you adapt, and you move forward with incomplete information - a familiar feeling for anyone who’s ever led a team through uncertainty.

There’s humility in that. You stop pretending you can anticipate everything. You learn to trust the systems (and yourself!) even when the map and the path disagree. You plan, but you prepare to adapt.

Corporate life rewards certainty: clear metrics, crisp plans, confident forecasts. But real progress rarely fits that mold. The best leaders I’ve known - and the kind I hope to continue being - navigate ambiguity easily without losing direction.

The trail gave me five months of practice in that.

Coming Home

Everyone asks, “How was the trail?” I usually smile and tell them that my legs and feet were done - but my mind was not.

But the truth is more complicated. It was beautiful and brutal and boring and life-changing, sometimes all in the same hour. It taught me resilience and persistence and growth in ways no leadership book ever could. It reminded me that progress isn’t always visible - that you can walk for days through burned forest before reaching new growth.

It also showed me that community can form instantly among strangers when everyone’s moving in the same direction. I’ve always valued (and leveraged) my community to help me grow in work, and I met utterly amazing people on trail who have changed who I am as a human being.

Now, back at home in the city, I’m trying to bring those lessons into a world that moves faster than it needs to. I still miss the trail. I still wake up early. I still walk a lot. And I still think about the people I met, their generosity, their kindness, and the way they changed me

Those experiences changed what I value.

The Next Climb

Over the coming weeks, I’ll be writing again - at some consistent pace, but definitely not weekly for a while. I want to write about what comes next: re-entry, leadership, work, and whatever other trails I find myself on.

I’ve spent most of my career focused on how teams work together - how we build trust, reduce friction, and help good people do great work. That hasn’t changed. The PCT reminded me of that.

I’m easing back into conversations about new opportunities. I’m not rushing, but I think I’m almost ready. Just as I felt many times this summer, I’m tired, grateful, and already curious about what tomorrow may look like.

If you’ve been reading my work for a while - thank you for sticking around during my brief sabbatical. If you’re new, welcome.

Either way, I hope what I share here helps you slow down, look up, and take the next step with a little more intention. The long trail back isn’t about returning to where you were. It’s about carrying forward what you’ve learned - and walking on.